scholarly journals Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers

2020 ◽  
Vol 11 (36) ◽  
pp. 10000-10004
Author(s):  
Faxiang Bu ◽  
Lijun Lu ◽  
Xia Hu ◽  
Shengchun Wang ◽  
Heng Zhang ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Oxidative Decarboxylation ◽  
Diaryl Ethers ◽  
Valuable Compounds

Carboxylic acid compounds are important chemicals and are widely present in various natural products. The conversion of carboxylic acids into valuable compounds is a promising field.

The Chemistry of Phthalide-3-carboxylic Acid. V. The Reaction of the Acid With Imines

1989 ◽  
Vol 42 (1) ◽  
pp. 49 ◽  
Author(s):  
J Chiefari ◽  
WK Janowski ◽  
RH Prager
Keyword(s):  
Natural Products ◽  
Carboxylic Acid ◽  
Acetic Anhydride ◽  
Dimethyl Sulfoxide ◽  
Carboxylic Acids ◽  
Dehydration Product

Phthalide-3-carboxylic acids decarboxylate readily in the presence of imines, the product depending on the solvent used. In dimethyl sulfoxide, or in the absence of solvent, at 130�, the product is the 3-alkyl 3-hydroxyisoindolone or its dehydration product, but in acetic anhydride at 130� the product is a mixture of diastereoisomeric 3-acetylarninoalkylphthalides. The reactions can be applied to the synthesis of natural products such as the isoindoloisoquinoline and phthalideisoquinoline alkaloids.

One Pot Conversion of Carboxylic Acid to Ketone Using Trimethylsilyl Chloride

2020 ◽  
Vol 07 ◽  
Author(s):  
Habtamu Gelaw Mekonnen ◽  
Samaresh Jana
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Organometallic Reagent ◽  
Trimethylsilyl Ester ◽  
Reaction Conditions ◽  
One Pot ◽  
Simple Process ◽  
Organolithium Reagents

Background: Ketone is abundant in many natural products and in pharmaceuticals. It is believed to be one of the important functional groups in organic chemistry. Till date,several research approaches have been made to access ketone from a readily available starting materials. One such notable transformation consists of the conversion of carboxylic acid to the corresponding ketone in a one pot manner. Objective: We aimed to develop a simple one pot reaction for the conversion of carboxylic acid to ketone. This reaction could be useful to convert all types of carboxylic acid to ketone in a facile manner. Methods: In this procedure, a carboxylic acid has been converted to the corresponding trimethylsilyl ester using trimethylsilyl chloride in the presence of a base. A suitable organometallic reagent can interact with the ester formed at 20°C to produce the corresponding ketone. Results: Under the optimized reaction conditions, various aromatic, aliphatic and heteroaromatic carboxylic acids have been converted to the corresponding ketones using organolithium reagents, in a one pot manner. Moderate to good yields of the desired ketones were observed in most of the transformations. Conclusion: Conversion of carboxylic acid to ketone has been reported in a one pot fashion, where carboxylic acid has been transformed to its silyl ester. Organolithium reagents were used as nucleophile for our reaction purpose, whereas the organomagnesium reagents were not useful for this transformation. Aliphatic, aromatic and heteroaromatic carboxylic acids have been converted to the ketones following a simple process.

The mechanism of lead tetraacetate decarboxylation. II. 2,3,3-Trimethylbutanoic and Adamantane-2-carboxylic acids

1974 ◽  
Vol 27 (8) ◽  
pp. 1693 ◽  
Author(s):  
ALJ Beckwith ◽  
RT Cross ◽  
GE Gream
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Major Product ◽  
Lead Tetraacetate ◽  
Oxidative Decarboxylation ◽  
Catalysed Reaction

Oxidative decarboxylation of 2,3,3-trimethylbutanoic acid with lead tetraacetate in benzene or acetic acid affords mainly 3,3-dimethylbut-2-yl acetate; the major product from the cupric salt catalysed reaction is 3,3-dimethylbut-1-ene. The low yields detected of rearrangement products provide evidence for the intermediacy of organolead and organocopper compounds which decompose by SNi displacement or cyclic cis-elimination. Other reactions discussed are oxidative decarboxylation of adamantane-2-carboxylic acid, deamination of 3,3-dimethylbut-2-ylamine, and thermolysis of bis(2,3,3-trimethylbutanoyl) peroxide and of t-butyl adamantane-2-percarboxylate. A reinterpretation of previous results on the oxidative decarboxylation of exo- and endo-nor- bornane-2-carboxylic acid with lead tetraacetate is presented.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

scholarly journals Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

2021 ◽  
pp. 174751982098715
Author(s):  
Khethobole C Sekgota ◽  
Michelle Isaacs ◽  
Heinrich C Hoppe ◽  
Ronnett Seldon ◽  
Digby F Warner ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Coupling Agent ◽  
Methyl Esters ◽  
Acid Anhydride

Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

scholarly journals Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications

Antioxidants ◽  
2021 ◽  
Vol 10 (4) ◽  
pp. 512
Author(s):  
Laurène Minsat ◽  
Cédric Peyrot ◽  
Fanny Brunissen ◽  
Jean-Hugues Renault ◽  
Florent Allais
Keyword(s):  
Natural Products ◽  
Consumer Demand ◽  
Radical Scavenging ◽  
Green Process ◽  
Direct Extraction ◽  
Low Concentration ◽  
Cosmetic Formulations ◽  
Valuable Compounds ◽  
The Stability

The current cosmetic and nutraceutical markets are characterized by a strong consumer demand for a return to natural products that are less harmful to both the consumers and the environment than current petrosourced products. Phloretin, a natural dihydrochalcone (DHC) found in apple, has been widely studied for many years and identified as a strong antioxidant and anti-tyrosinase ingredient for cosmetic formulations. Its low concentration in apples does not allow it to be obtained by direct extraction from biomass in large quantities to meet market volumes and prices. Moreover, its remarkable structure prevents its synthesis through a green process. To overcome these issues, the synthesis of phloretin analogs appears as an alternative to access valuable compounds that are potentially more active than phloretin itself. Under such considerations, 12 chalcones (CHs) and 12 dihydrochalcones (DHCs) were synthesized through a green Claisen–Schmidt condensation using bio-based reagents. In order to evaluate the potential of these molecules, radical scavenging DPPH and anti-tyrosinase tests have been conducted. Moreover, the UV filtering properties and the stability of these analogs towards UV-radiations have been evaluated. Some molecules showed competitive antioxidant and anti-tyrosinase activities regarding phloretin. Two compounds in particular showed EC50 lower than phloretin, one chalcone and one dihydrochalcone.

scholarly journals Mechanically induced solvent-free esterification method at room temperature

RSC Advances ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 5080-5085
Author(s):  
Lei Zheng ◽  
Chen Sun ◽  
Wenhao Xu ◽  
Alexandr V. Dushkin ◽  
Nikolay Polyakov ◽  
...  
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Late Stage ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Solvent Free ◽  
Mild Conditions

We have developed I2/KH2PO2 and KI/P(OEt)3 strategy syntheses of esters from carboxylic acids and alcohols through different reaction mechanisms. The advantages of present protocol: mild conditions and late-stage diversification of natural products.

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